catena-Poly[[(1,10-phenanthroline-κ2N,N′)praseodymium(III)]-di-μ-phenoxy­acetato-κ4O:O′-[(1,10-phenanthroline-κ2N,N′)praseodymium(III)]-di-μ-phenoxy­acetato-κ4O:O′-di-μ-phenoxy­acetato-κ3O,O′:O;κ3O:O,O′]

Zhong, H.; Yang, X.-M.; Luo, Q.-Y.; Xu, Y.-P.

doi:10.1107/S1600536807068614

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages m317-m318

doi:10.1107/S1600536807068614

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: catena-Poly[[(1,10-phenanthroline-κ²N,N′)praseodymium(III)]-di-μ-phenoxyacetato-κ⁴O:O′-[(1,10-phenanthroline-κ²N,N′)praseodymium(III)]-di-μ-phenoxyacetato-κ⁴O:O′-di-μ-phenoxyacetato-κ³O,O′:O;κ³O:O,O′]

H. Zhong,^a ^* X.-M. Yang,^b Q.-Y. Luo ^a and Y.-P. Xu ^a

^aCollege of Chemistry and Chemical Engineering, Provincial Key Laboratory of Coordination Chemistry, Jinggangshan University, Jian 343009, People's Republic of China, and ^bInstitute of Applied Materials, Jiangxi University of Finance and Economics, Nanchang 330032, People's Republic of China
^*Correspondence e-mail: huazhong06@126.com

(Received 15 May 2007; accepted 28 December 2007; online 9 January 2008)

The title complex, [Pr₂(C₈H₇O₃)₆(C₁₂H₈N₂)₂]_n, which has an inversion centre midway between the two Pr^III atoms of the structural unit, forms a one-dimensional polymer bridged alternately by either two bidentate, or two bidentate and two terdentate, phenoxyacetate carboxylate groups. Each Pr^III atom is thus nine-coordinated by two N atoms of a 1,10-phenanthroline ligand and seven O atoms from six phenoxyacetate ligands. The coordination geometry at the Pr^III atom is distorted tricapped trigonal prismatic. One phenyl ring is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Related literature

For related literature, see: Allen et al. (1987 ); Daiguebonne et al. (2000 ); Farrugia et al. (2000 ); Kay et al. (1972 ); Ma et al. (1999 ); Mao et al. (1998 ); Starynowicz (1991 , 1993 ); Tsukube & Shinoda (2002 ); Zhang et al. (2005 ); Zeng et al. (2000 ); Zhong et al. (2007 ).

Experimental

Crystal data

[Pr₂(C₈H₇O₃)₆(C₁₂H₈N₂)₂]
M_r = 1549.04
Monoclinic, P 2₁ /n
a = 20.204 (4) Å
b = 8.499 (4) Å
c = 20.799 (3) Å
β = 107.198 (6)°
V = 3411.8 (17) Å³
Z = 2
Mo Kα radiation
μ = 1.49 mm⁻¹
T = 273 (2) K
0.33 × 0.12 × 0.08 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.642, T_max = 0.890
27763 measured reflections
7712 independent reflections
5037 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 0.90
7712 reflections
452 parameters
144 restraints
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Pr1—O1	2.489 (2)
Pr1—O2ⁱ	2.535 (2)
Pr1—O4	2.565 (2)
Pr1—O5	2.817 (3)
Pr1—O5ⁱ	2.449 (2)
Pr1—O7	2.409 (3)
Pr1—O8ⁱⁱ	2.545 (3)
Pr1—N1	2.753 (3)
Pr1—N2	2.720 (3)

O1—Pr1—O4	73.62 (8)
O1—Pr1—O5	65.11 (8)
O1—Pr1—O7	145.88 (9)
O4—Pr1—O5	48.17 (8)
O4—Pr1—O7	138.84 (9)
O5—Pr1—O7	139.57 (8)
O1—Pr1—N1	127.55 (9)
O4—Pr1—N1	63.48 (9)
O5—Pr1—N1	102.34 (9)
O7—Pr1—N1	77.09 (9)
O1—Pr1—N2	81.11 (9)
O4—Pr1—N2	74.08 (9)
O5—Pr1—N2	118.22 (8)
O7—Pr1—N2	96.74 (9)
N1—Pr1—N2	59.78 (10)
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+2, -y+1, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	0.93	2.46	3.147 (5)	130
C10—H10⋯O4ⁱⁱⁱ	0.93	2.34	3.211 (5)	156
C12—H12⋯O8ⁱⁱ	0.93	2.47	3.063 (5)	122
C22—H22B⋯O7^iv	0.97	2.41	3.353 (5)	166
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+2, -y+1, -z+2; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x, y-1, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068614/rt2009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068614/rt2009Isup2.hkl

checkCIF report

Comment top

In recent years, there has been great interest in the synthesis of metal organic frameworks (MOFs) with organic ligands and rare earth metals because of their novel structures, fascinating properties and important roles in special materials with potential optical, electronic, magnetic and biological applications (Daiguebonne et al., 2000; Farrugia et al., 2000; Tsukube & Shinoda, 2002; Zhang et al., 2005). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Starynowicz, 1991, 1993; Kay et al., 1972; Ma et al., 1999; Zeng et al., 2000; Mao et al., 1998). We report herein the crystal structure of the title compound, (I).

In the molecular unit of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The Pr^III metal centres are bridged alternatively either by two bidentate, or by two terdentate and two bidentate, phenoxyacetato carboxylate groups with an inversion centre between them. Each Pr atom is nine-coordinated by two N atoms of the 1,10-phenanthroline ligand and seven O atoms from six phenoxyacetate ligands (Table 1), and the coordination geometry at the Pr atom forms a tricapped trigonal prism. The Pr—O bond lengths are in the range 2.409 (3) to 2.817 (3) Å. The Pr—N bond lengths are in the range 2.720 (3) to 2.753 (3) Å. Hydrogen bonds between C—H groups and O atoms of neighbouring phenoxyacetate ligands, with C···O distances of 3.063 (5) to 3.353 (5) Å, generate a layered hydrogen-bonded network (Table 2).

Related literature top

For related literature, see: Allen et al. (1987); Daiguebonne et al. (2000); Farrugia et al. (2000); Kay et al. (1972); Ma et al. (1999); Mao et al. (1998); Starynowicz (1991, 1993); Tsukube & Shinoda (2002); Zhang et al. (2005); Zeng et al. (2000); Zhong et al. (2007).

Experimental top

The title compound was synthesized using the hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Praseodymium(III) chloride hexahydrate (71.1 mg, 0.2 mmol), 1,10-phenanthroline (39.6 mg, 0.2 mmol), phenoxyacetic acid (91.3 mg, 0.6 mmol), sodium hydroxide (24 mg, 0.6 mmol) and distilled water (4 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure for 7 d at 413 K and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small green crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature (yield: 72.7 mg, 36%).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level [for symmetry codes, see Tabel 1]. All H atoms have been omitted for clarity.
	Fig. 2. View along the b axis showing one dimensional polymeric structure, linked by H-bonding.

catena-Poly[[(1,10-phenanthroline-κ²N,N')praseodymium(III)]- di-µ-phenoxyacetato-κ⁴O:O'-[(1,10-phenanthroline- κ²N,N')praseodymium(III)]-di-µ-phenoxyacetato-κ⁴O:O'-di-µ- phenoxyacetato-κ³O,O':O;κ³O:O,O'] top

Crystal data top

[Pr₂(C₈H₇O₃)₆(C₁₂H₈N₂)₂]	F(000) = 1560
M_r = 1549.04	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9075 reflections
a = 20.204 (4) Å	θ = 2.4–26.9°
b = 8.499 (4) Å	µ = 1.49 mm⁻¹
c = 20.799 (3) Å	T = 273 K
β = 107.198 (6)°	Needle, green
V = 3411.8 (17) Å³	0.33 × 0.12 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII area-detector diffractometer	7712 independent reflections
Radiation source: fine-focus sealed tube	5037 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→25
T_min = 0.642, T_max = 0.891	k = −10→11
27763 measured reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0573P)² + 0.9707P] where P = (F_o² + 2F_c²)/3
7712 reflections	(Δ/σ)_max = 0.002
452 parameters	Δρ_max = 1.04 e Å⁻³
144 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[Pr₂(C₈H₇O₃)₆(C₁₂H₈N₂)₂]	V = 3411.8 (17) Å³
M_r = 1549.04	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 20.204 (4) Å	µ = 1.49 mm⁻¹
b = 8.499 (4) Å	T = 273 K
c = 20.799 (3) Å	0.33 × 0.12 × 0.08 mm
β = 107.198 (6)°

Data collection top

Bruker APEXII area-detector diffractometer	7712 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5037 reflections with I > 2σ(I)
T_min = 0.642, T_max = 0.891	R_int = 0.043
27763 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	144 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.90	Δρ_max = 1.04 e Å⁻³
7712 reflections	Δρ_min = −0.64 e Å⁻³
452 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pr1	0.931206 (10)	0.19065 (2)	0.964285 (9)	0.03966 (8)
O1	0.97069 (13)	0.0604 (3)	0.87489 (11)	0.0491 (6)
O2	1.06691 (13)	−0.0826 (3)	0.92159 (12)	0.0516 (6)
O3	1.11827 (15)	−0.0166 (4)	0.82183 (14)	0.0691 (8)
O4	0.84633 (12)	−0.0358 (3)	0.91883 (12)	0.0466 (6)
O5	0.94657 (13)	−0.1383 (3)	0.97718 (12)	0.0518 (7)
O6	0.78462 (16)	−0.3257 (3)	0.89785 (16)	0.0648 (8)
O7	0.94001 (13)	0.4205 (3)	1.03407 (12)	0.0500 (6)
O8	1.00785 (15)	0.6123 (3)	1.09093 (12)	0.0590 (7)
O9	0.98717 (16)	0.5273 (3)	1.20640 (13)	0.0645 (8)
N1	0.79697 (17)	0.2344 (4)	0.96683 (16)	0.0506 (8)
N2	0.83406 (18)	0.3071 (3)	0.85447 (15)	0.0498 (8)
C1	0.7781 (2)	0.1926 (5)	1.0199 (2)	0.0643 (12)
H1	0.8126	0.1707	1.0598	0.077*
C2	0.7089 (3)	0.1797 (6)	1.0195 (3)	0.0840 (16)
H2	0.6978	0.1495	1.0580	0.101*
C3	0.6575 (3)	0.2127 (7)	0.9606 (4)	0.0962 (19)
H3	0.6112	0.2043	0.9591	0.115*
C4	0.6746 (2)	0.2581 (7)	0.9041 (3)	0.0772 (14)
C5	0.7458 (2)	0.2679 (5)	0.9084 (2)	0.0541 (10)
C6	0.6231 (3)	0.2967 (8)	0.8409 (4)	0.111 (2)
H6	0.5763	0.2879	0.8372	0.133*
C7	0.6424 (3)	0.3448 (8)	0.7880 (3)	0.106 (2)
H7	0.6085	0.3727	0.7487	0.127*
C8	0.7134 (3)	0.3547 (6)	0.7899 (2)	0.0727 (14)
C9	0.7660 (2)	0.3102 (4)	0.8506 (2)	0.0536 (10)
C10	0.7358 (3)	0.4037 (6)	0.7367 (2)	0.0878 (17)
H10	0.7036	0.4392	0.6975	0.105*
C11	0.8031 (3)	0.4012 (6)	0.7405 (2)	0.0819 (15)
H11	0.8175	0.4331	0.7040	0.098*
C12	0.8524 (3)	0.3492 (5)	0.8009 (2)	0.0644 (12)
H12	0.8989	0.3448	0.8028	0.077*
C13	1.0286 (2)	0.0032 (4)	0.87703 (17)	0.0442 (9)
C14	1.0524 (2)	0.0512 (5)	0.81759 (19)	0.0564 (10)
H14A	1.0186	0.0170	0.7763	0.068*
H14B	1.0557	0.1649	0.8163	0.068*
C15	1.1460 (2)	0.0142 (6)	0.7704 (2)	0.0646 (12)
C16	1.2081 (3)	−0.0565 (7)	0.7766 (3)	0.0808 (14)
H16	1.2289	−0.1179	0.8141	0.097*
C17	1.2403 (3)	−0.0368 (7)	0.7268 (3)	0.0955 (18)
H17	1.2827	−0.0850	0.7309	0.115*
C18	1.2101 (4)	0.0526 (7)	0.6722 (3)	0.104 (2)
H18	1.2318	0.0650	0.6388	0.124*
C19	1.1491 (4)	0.1238 (8)	0.6659 (3)	0.109 (2)
H19	1.1291	0.1856	0.6282	0.130*
C20	1.1148 (3)	0.1059 (7)	0.7157 (3)	0.0847 (16)
H20	1.0725	0.1548	0.7114	0.102*
C21	0.8840 (2)	−0.1509 (5)	0.93913 (18)	0.0457 (9)
C22	0.8576 (2)	−0.3140 (5)	0.9189 (2)	0.0573 (10)
H22A	0.8750	−0.3490	0.8825	0.069*
H22B	0.8760	−0.3842	0.9567	0.069*
C23A	0.75531 (19)	−0.3041 (3)	0.9521 (2)	0.079 (6)	0.384 (14)
C24A	0.79664 (17)	−0.2697 (2)	1.0169 (2)	0.076 (5)	0.384 (14)
C25A	0.7671 (2)	−0.2571 (3)	1.0691 (2)	0.101 (6)	0.384 (14)
C26A	0.6962 (3)	−0.2790 (4)	1.0566 (3)	0.110 (6)	0.384 (14)
C27A	0.65490 (19)	−0.3133 (3)	0.9918 (3)	0.126 (7)	0.384 (14)
C28A	0.68444 (18)	−0.3259 (3)	0.9396 (2)	0.120 (6)	0.384 (14)
C23B	0.7508 (2)	−0.3175 (3)	0.9425 (2)	0.077 (4)	0.616 (14)
C24B	0.77565 (17)	−0.2805 (2)	1.0105 (2)	0.112 (4)	0.616 (14)
C25B	0.7302 (2)	−0.2706 (3)	1.0492 (2)	0.120 (4)	0.616 (14)
C26B	0.6599 (2)	−0.2977 (4)	1.0198 (3)	0.133 (5)	0.616 (14)
C27B	0.63499 (18)	−0.3347 (3)	0.9518 (3)	0.115 (4)	0.616 (14)
C28B	0.6804 (2)	−0.3446 (3)	0.9132 (2)	0.086 (3)	0.616 (14)
C29	0.96861 (15)	0.4991 (3)	1.08649 (13)	0.0453 (9)
C30	0.94968 (19)	0.4431 (3)	1.14756 (13)	0.0583 (11)
H30A	0.9004	0.4574	1.1402	0.070*
H30B	0.9598	0.3316	1.1542	0.070*
C31	0.9746 (2)	0.4891 (5)	1.26544 (19)	0.0558 (10)
C32	1.0143 (3)	0.5695 (6)	1.3220 (2)	0.0749 (13)
H32	1.0474	0.6418	1.3181	0.090*
C33	1.0046 (3)	0.5419 (7)	1.3836 (2)	0.0929 (17)
H33	1.0306	0.5969	1.4212	0.111*
C34	0.9565 (3)	0.4332 (9)	1.3897 (3)	0.108 (2)
H34	0.9492	0.4153	1.4312	0.130*
C35	0.9196 (3)	0.3522 (8)	1.3342 (3)	0.108 (2)
H35	0.8879	0.2765	1.3386	0.129*
C36	0.9279 (2)	0.3792 (7)	1.2721 (2)	0.0743 (14)
H36	0.9019	0.3230	1.2348	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pr1	0.04654 (13)	0.03356 (12)	0.03391 (11)	−0.00161 (9)	0.00420 (8)	0.00057 (9)
O1	0.0588 (16)	0.0479 (16)	0.0398 (14)	0.0067 (13)	0.0132 (12)	0.0022 (12)
O2	0.0634 (16)	0.0494 (16)	0.0428 (14)	0.0069 (14)	0.0167 (12)	0.0097 (12)
O3	0.0709 (19)	0.085 (2)	0.0591 (18)	0.0162 (17)	0.0304 (15)	0.0209 (16)
O4	0.0480 (14)	0.0350 (15)	0.0484 (14)	0.0008 (12)	0.0015 (11)	−0.0027 (11)
O5	0.0480 (15)	0.0524 (16)	0.0462 (15)	−0.0032 (12)	0.0003 (12)	0.0071 (12)
O6	0.0616 (19)	0.0474 (18)	0.073 (2)	−0.0128 (14)	0.0006 (15)	−0.0080 (15)
O7	0.0718 (17)	0.0341 (14)	0.0424 (14)	−0.0063 (13)	0.0142 (12)	−0.0043 (11)
O8	0.087 (2)	0.0515 (18)	0.0383 (14)	−0.0250 (16)	0.0177 (13)	−0.0031 (12)
O9	0.091 (2)	0.0617 (19)	0.0416 (15)	−0.0270 (16)	0.0210 (14)	−0.0058 (13)
N1	0.0508 (19)	0.0435 (19)	0.0498 (19)	0.0053 (15)	0.0029 (15)	−0.0074 (15)
N2	0.065 (2)	0.0375 (18)	0.0373 (17)	0.0016 (16)	−0.0006 (14)	0.0005 (14)
C1	0.059 (3)	0.075 (3)	0.058 (3)	0.008 (2)	0.015 (2)	−0.002 (2)
C2	0.064 (3)	0.111 (5)	0.084 (4)	0.003 (3)	0.032 (3)	−0.011 (3)
C3	0.049 (3)	0.109 (5)	0.128 (5)	−0.002 (3)	0.022 (3)	−0.018 (4)
C4	0.053 (3)	0.088 (4)	0.076 (4)	0.007 (3)	−0.004 (2)	−0.016 (3)
C5	0.052 (2)	0.039 (2)	0.061 (3)	0.0057 (18)	0.0014 (19)	−0.0115 (18)
C6	0.060 (3)	0.131 (6)	0.114 (5)	0.018 (3)	−0.017 (3)	−0.027 (5)
C7	0.080 (4)	0.113 (5)	0.087 (4)	0.039 (4)	−0.034 (3)	−0.019 (4)
C8	0.077 (3)	0.061 (3)	0.056 (3)	0.018 (2)	−0.017 (2)	−0.011 (2)
C9	0.060 (2)	0.035 (2)	0.048 (2)	0.0049 (19)	−0.0111 (18)	−0.0053 (17)
C10	0.117 (5)	0.071 (4)	0.047 (3)	0.018 (3)	−0.020 (3)	0.000 (2)
C11	0.122 (5)	0.070 (4)	0.040 (2)	−0.001 (3)	0.003 (3)	0.009 (2)
C12	0.084 (3)	0.051 (3)	0.048 (2)	−0.003 (2)	0.004 (2)	0.0067 (19)
C13	0.058 (2)	0.035 (2)	0.038 (2)	−0.0060 (18)	0.0116 (17)	−0.0025 (15)
C14	0.066 (3)	0.056 (3)	0.049 (2)	0.006 (2)	0.0199 (19)	0.0123 (19)
C15	0.075 (3)	0.067 (3)	0.061 (3)	−0.006 (2)	0.034 (2)	0.002 (2)
C16	0.079 (3)	0.098 (4)	0.075 (3)	0.001 (3)	0.038 (3)	0.002 (3)
C17	0.092 (4)	0.100 (5)	0.113 (5)	−0.002 (4)	0.060 (4)	−0.006 (4)
C18	0.135 (5)	0.087 (4)	0.124 (5)	−0.015 (4)	0.092 (5)	−0.007 (4)
C19	0.159 (6)	0.101 (5)	0.092 (4)	0.008 (5)	0.077 (4)	0.026 (4)
C20	0.103 (4)	0.088 (4)	0.080 (3)	0.010 (3)	0.053 (3)	0.024 (3)
C21	0.051 (2)	0.050 (2)	0.0325 (18)	−0.0054 (18)	0.0066 (16)	−0.0032 (16)
C22	0.062 (3)	0.045 (2)	0.058 (3)	0.002 (2)	0.008 (2)	−0.0060 (19)
C23A	0.090 (12)	0.047 (10)	0.126 (11)	−0.009 (9)	0.071 (9)	0.027 (9)
C24A	0.116 (10)	0.055 (9)	0.086 (9)	−0.011 (7)	0.073 (8)	0.000 (7)
C25A	0.118 (11)	0.079 (10)	0.127 (11)	0.017 (8)	0.069 (9)	0.021 (9)
C26A	0.109 (12)	0.111 (11)	0.140 (12)	0.047 (9)	0.082 (10)	0.052 (9)
C27A	0.103 (11)	0.138 (13)	0.168 (14)	0.041 (10)	0.087 (9)	0.065 (11)
C28A	0.102 (12)	0.113 (12)	0.167 (13)	0.032 (10)	0.074 (10)	0.046 (10)
C23B	0.083 (8)	0.033 (6)	0.107 (8)	0.002 (5)	0.016 (6)	−0.005 (6)
C24B	0.145 (9)	0.086 (8)	0.109 (9)	−0.021 (7)	0.044 (7)	0.012 (7)
C25B	0.144 (10)	0.120 (9)	0.117 (9)	0.000 (8)	0.070 (8)	0.028 (7)
C26B	0.145 (10)	0.128 (10)	0.140 (10)	0.041 (9)	0.063 (9)	0.023 (8)
C27B	0.123 (8)	0.086 (7)	0.141 (9)	0.033 (6)	0.047 (7)	0.016 (7)
C28B	0.079 (6)	0.056 (6)	0.133 (8)	0.014 (5)	0.046 (5)	0.012 (5)
C29	0.061 (2)	0.033 (2)	0.040 (2)	−0.0035 (18)	0.0133 (17)	0.0007 (16)
C30	0.077 (3)	0.055 (3)	0.044 (2)	−0.020 (2)	0.0193 (19)	−0.0057 (19)
C31	0.072 (3)	0.056 (3)	0.038 (2)	−0.003 (2)	0.0146 (19)	0.0016 (18)
C32	0.092 (3)	0.077 (3)	0.054 (3)	−0.019 (3)	0.017 (2)	−0.009 (2)
C33	0.122 (5)	0.108 (5)	0.042 (3)	−0.021 (4)	0.014 (3)	−0.009 (3)
C34	0.133 (5)	0.146 (6)	0.055 (3)	−0.031 (5)	0.043 (3)	0.009 (4)
C35	0.124 (5)	0.141 (6)	0.066 (4)	−0.059 (4)	0.041 (3)	−0.003 (4)
C36	0.081 (3)	0.091 (4)	0.053 (3)	−0.033 (3)	0.023 (2)	−0.003 (2)

Geometric parameters (Å, º) top

Pr1—O1	2.489 (2)	C15—C20	1.370 (6)
Pr1—O2ⁱ	2.535 (2)	C16—C17	1.387 (7)
Pr1—O4	2.565 (2)	C16—H16	0.9300
Pr1—O5	2.817 (3)	C17—C18	1.352 (8)
Pr1—O5ⁱ	2.449 (2)	C17—H17	0.9300
Pr1—O7	2.409 (3)	C18—C19	1.345 (8)
Pr1—O8ⁱⁱ	2.545 (3)	C18—H18	0.9300
Pr1—N1	2.753 (3)	C19—C20	1.415 (7)
Pr1—N2	2.720 (3)	C19—H19	0.9300
O1—C13	1.255 (4)	C20—H20	0.9300
O2—C13	1.252 (4)	C21—C22	1.500 (5)
O2—Pr1ⁱ	2.535 (2)	C22—H22A	0.9700
O3—C15	1.372 (5)	C22—H22B	0.9700
O3—C14	1.429 (5)	C23A—C24B	1.1792
O4—C21	1.235 (4)	C23A—C24A	1.3900
O5—C21	1.282 (4)	C23A—C28A	1.3900
O5—Pr1ⁱ	2.449 (2)	C23A—C28B	1.5294
O6—C23B	1.309 (5)	C24A—C25A	1.3900
O6—C22	1.412 (5)	C24A—C23B	1.6025
O6—C23A	1.433 (5)	C24A—C25B	1.6693
O7—C29	1.263 (3)	C25A—C25B	0.7471
O8—C29	1.233 (3)	C25A—C24B	1.2955
O8—Pr1ⁱⁱ	2.545 (3)	C25A—C26A	1.3900
O9—C31	1.364 (5)	C26A—C25B	0.7502
O9—C30	1.427 (4)	C26A—C26B	0.9047
N1—C1	1.319 (5)	C26A—C27A	1.3900
N1—C5	1.372 (5)	C27A—C26B	0.5756
N2—C12	1.323 (5)	C27A—C27B	0.8310
N2—C9	1.355 (5)	C27A—C28A	1.3900
C1—C2	1.401 (6)	C27A—C25B	1.6721
C1—H1	0.9300	C28A—C28B	0.5549
C2—C3	1.381 (8)	C28A—C27B	1.1036
C2—H2	0.9300	C28A—C23B	1.3252
C3—C4	1.373 (8)	C23B—C24B	1.3900
C3—H3	0.9300	C23B—C28B	1.3900
C4—C5	1.418 (6)	C24B—C25B	1.3900
C4—C6	1.452 (8)	C25B—C26B	1.3900
C5—C9	1.424 (6)	C26B—C27B	1.3900
C6—C7	1.335 (9)	C27B—C28B	1.3900
C6—H6	0.9300	C29—C30	1.5078
C7—C8	1.426 (8)	C30—H30A	0.9700
C7—H7	0.9300	C30—H30B	0.9700
C8—C10	1.377 (7)	C31—C36	1.364 (6)
C8—C9	1.440 (5)	C31—C32	1.391 (6)
C10—C11	1.340 (7)	C32—C33	1.372 (6)
C10—H10	0.9300	C32—H32	0.9300
C11—C12	1.423 (6)	C33—C34	1.374 (8)
C11—H11	0.9300	C33—H33	0.9300
C12—H12	0.9300	C34—C35	1.361 (8)
C13—C14	1.509 (5)	C34—H34	0.9300
C14—H14A	0.9700	C35—C36	1.371 (6)
C14—H14B	0.9700	C35—H35	0.9300
C15—C16	1.363 (6)	C36—H36	0.9300

O1—Pr1—O4	73.62 (8)	C21—C22—H22A	108.8
O1—Pr1—O5	65.11 (8)	O6—C22—H22B	108.8
O1—Pr1—O7	145.88 (9)	C21—C22—H22B	108.8
O4—Pr1—O5	48.17 (8)	H22A—C22—H22B	107.7
O4—Pr1—O7	138.84 (9)	C24B—C23A—C28A	104.0
O5—Pr1—O7	139.57 (8)	C24A—C23A—C28A	120.0
O1—Pr1—N1	127.55 (9)	C24B—C23A—O6	137.2 (2)
O4—Pr1—N1	63.48 (9)	C24A—C23A—O6	121.4 (2)
O5—Pr1—N1	102.34 (9)	C28A—C23A—O6	118.6 (2)
O7—Pr1—N1	77.09 (9)	C24B—C23A—C28B	125.0
O1—Pr1—N2	81.11 (9)	C24A—C23A—C28B	141.0
O4—Pr1—N2	74.08 (9)	O6—C23A—C28B	97.4 (2)
O5—Pr1—N2	118.22 (8)	C23A—C24A—C25A	120.0
O7—Pr1—N2	96.74 (9)	C25A—C24A—C23B	121.0
N1—Pr1—N2	59.78 (10)	C23A—C24A—C25B	93.7
O7—Pr1—O5ⁱ	87.92 (9)	C23B—C24A—C25B	94.7
O5ⁱ—Pr1—O1	77.99 (9)	C25B—C25A—C24B	81.0
O7—Pr1—O2ⁱ	75.61 (8)	C24B—C25A—C26A	102.7
O5ⁱ—Pr1—O2ⁱ	74.63 (8)	C25B—C25A—C24A	98.2
O1—Pr1—O2ⁱ	128.25 (9)	C26A—C25A—C24A	120.0
O7—Pr1—O8ⁱⁱ	77.23 (9)	C25B—C26A—C26B	113.9
O5ⁱ—Pr1—O8ⁱⁱ	78.03 (9)	C26B—C26A—C25A	135.7
O1—Pr1—O8ⁱⁱ	69.56 (9)	C25B—C26A—C27A	98.3
O2ⁱ—Pr1—O8ⁱⁱ	141.78 (8)	C25A—C26A—C27A	120.0
O5ⁱ—Pr1—O4	120.85 (9)	C26B—C27A—C27B	162.1
O2ⁱ—Pr1—O4	84.07 (8)	C26B—C27A—C28A	145.1
O8ⁱⁱ—Pr1—O4	133.42 (8)	C27B—C27A—C28A	52.6
O5ⁱ—Pr1—N2	148.71 (10)	C27B—C27A—C26A	172.5
O2ⁱ—Pr1—N2	136.51 (10)	C28A—C27A—C26A	120.0
O8ⁱⁱ—Pr1—N2	72.96 (10)	C26B—C27A—C25B	51.6
O5ⁱ—Pr1—N1	150.33 (9)	C27B—C27A—C25B	146.2
O2ⁱ—Pr1—N1	76.88 (9)	C28A—C27A—C25B	93.7
O8ⁱⁱ—Pr1—N1	122.05 (10)	C26B—C27A—C28B	154.6
O5ⁱ—Pr1—O5	72.90 (10)	C26A—C27A—C28B	129.4
O2ⁱ—Pr1—O5	65.21 (8)	C25B—C27A—C28B	103.1
O8ⁱⁱ—Pr1—O5	129.91 (9)	C28B—C28A—C27B	109.4
C13—O1—Pr1	130.3 (2)	C28B—C28A—C23B	84.9
C13—O2—Pr1ⁱ	137.7 (2)	C27B—C28A—C23B	164.8
C15—O3—C14	117.6 (3)	C28B—C28A—C27A	145.7
C21—O4—Pr1	101.0 (2)	C23B—C28A—C27A	128.5
C21—O5—Pr1ⁱ	163.1 (3)	C28B—C28A—C23A	93.7
C21—O5—Pr1	87.9 (2)	C27B—C28A—C23A	156.7
Pr1ⁱ—O5—Pr1	107.10 (9)	C27A—C28A—C23A	120.0
C23B—O6—C22	119.6 (3)	C28B—C28A—C26B	155.7
C22—O6—C23A	112.6 (3)	C27B—C28A—C26B	46.7
C29—O7—Pr1	151.9 (2)	C23B—C28A—C26B	118.6
C29—O8—Pr1ⁱⁱ	150.0 (2)	C23A—C28A—C26B	110.0
C31—O9—C30	117.4 (3)	C28B—C28A—C24B	127.6
C1—N1—C5	118.0 (4)	C27B—C28A—C24B	122.4
C1—N1—Pr1	120.6 (3)	C27A—C28A—C24B	85.7
C5—N1—Pr1	119.9 (3)	C26B—C28A—C24B	75.7
C12—N2—C9	118.5 (3)	O6—C23B—C28A	134.3 (3)
C12—N2—Pr1	119.6 (3)	O6—C23B—C24B	128.8 (2)
C9—N2—Pr1	121.6 (2)	C28A—C23B—C24B	96.6
N1—C1—C2	123.4 (4)	O6—C23B—C28B	111.1 (3)
N1—C1—H1	118.3	C24B—C23B—C28B	120.0
C2—C1—H1	118.3	O6—C23B—C24A	115.1 (2)
C3—C2—C1	118.4 (5)	C28A—C23B—C24A	110.3
C3—C2—H2	120.8	C28B—C23B—C24A	133.7
C1—C2—H2	120.8	C23A—C24B—C25A	153.2
C4—C3—C2	120.3 (5)	C25A—C24B—C23B	152.0
C4—C3—H3	119.9	C23A—C24B—C25B	121.2
C2—C3—H3	119.9	C23B—C24B—C25B	120.0
C3—C4—C5	118.0 (5)	C25A—C24B—C28A	111.6
C3—C4—C6	123.0 (6)	C25B—C24B—C28A	79.6
C5—C4—C6	119.1 (6)	C25A—C25B—C26A	136.4
N1—C5—C4	121.9 (4)	C25A—C25B—C24B	67.0
N1—C5—C9	118.2 (4)	C26A—C25B—C24B	156.1
C4—C5—C9	120.0 (4)	C25A—C25B—C26B	172.8
C7—C6—C4	120.7 (6)	C24B—C25B—C26B	120.0
C7—C6—H6	119.7	C25A—C25B—C24A	55.5
C4—C6—H6	119.7	C26A—C25B—C24A	167.7
C6—C7—C8	122.1 (5)	C26B—C25B—C24A	131.5
C6—C7—H7	118.9	C25A—C25B—C27A	167.8
C8—C7—H7	118.9	C26A—C25B—C27A	55.3
C10—C8—C7	124.2 (5)	C24B—C25B—C27A	101.1
C10—C8—C9	116.9 (5)	C24A—C25B—C27A	112.6
C7—C8—C9	118.9 (5)	C27A—C26B—C26A	138.7
N2—C9—C5	118.9 (3)	C26A—C26B—C27B	149.3
N2—C9—C8	121.9 (4)	C27A—C26B—C25B	109.4
C5—C9—C8	119.1 (4)	C27B—C26B—C25B	120.0
C11—C10—C8	121.1 (4)	C26A—C26B—C28A	114.2
C11—C10—H10	119.5	C25B—C26B—C28A	84.7
C8—C10—H10	119.5	C27A—C27B—C28A	90.7
C10—C11—C12	119.4 (5)	C28A—C27B—C26B	98.0
C10—C11—H11	120.3	C27A—C27B—C28B	112.7
C12—C11—H11	120.3	C26B—C27B—C28B	120.0
N2—C12—C11	122.0 (5)	C28A—C28B—C27B	48.5
N2—C12—H12	119.0	C28A—C28B—C23B	71.7
C11—C12—H12	119.0	C27B—C28B—C23B	120.0
O2—C13—O1	128.2 (3)	C28A—C28B—C23A	65.1
O2—C13—C14	119.1 (4)	C27B—C28B—C23A	113.5
O1—C13—C14	112.7 (3)	C23B—C28B—C27A	95.9
O3—C14—C13	110.9 (3)	C23A—C28B—C27A	89.4
O3—C14—H14A	109.5	O8—C29—O7	126.7 (3)
C13—C14—H14A	109.5	O8—C29—C30	120.06 (18)
O3—C14—H14B	109.5	O7—C29—C30	113.28 (15)
C13—C14—H14B	109.5	O9—C30—C29	111.20 (18)
H14A—C14—H14B	108.0	O9—C30—H30A	109.4
C16—C15—C20	120.9 (4)	C29—C30—H30A	109.4
C16—C15—O3	114.8 (4)	O9—C30—H30B	109.4
C20—C15—O3	124.3 (4)	C29—C30—H30B	109.4
C15—C16—C17	119.9 (5)	H30A—C30—H30B	108.0
C15—C16—H16	120.0	C36—C31—O9	124.9 (4)
C17—C16—H16	120.0	C36—C31—C32	119.6 (4)
C18—C17—C16	120.0 (6)	O9—C31—C32	115.5 (4)
C18—C17—H17	120.0	C33—C32—C31	120.0 (5)
C16—C17—H17	120.0	C33—C32—H32	120.0
C19—C18—C17	120.5 (5)	C31—C32—H32	120.0
C19—C18—H18	119.7	C32—C33—C34	120.1 (5)
C17—C18—H18	119.7	C32—C33—H33	119.9
C18—C19—C20	120.9 (6)	C34—C33—H33	119.9
C18—C19—H19	119.5	C35—C34—C33	119.1 (5)
C20—C19—H19	119.5	C35—C34—H34	120.5
C15—C20—C19	117.7 (5)	C33—C34—H34	120.5
C15—C20—H20	121.2	C34—C35—C36	121.7 (5)
C19—C20—H20	121.2	C34—C35—H35	119.1
O4—C21—O5	122.8 (3)	C36—C35—H35	119.1
O4—C21—C22	120.2 (3)	C31—C36—C35	119.4 (5)
O5—C21—C22	117.0 (4)	C31—C36—H36	120.3
O6—C22—C21	113.9 (3)	C35—C36—H36	120.3
O6—C22—H22A	108.8

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.93	2.46	3.147 (5)	130
C10—H10···O4ⁱⁱⁱ	0.93	2.34	3.211 (5)	156
C12—H12···O8ⁱⁱ	0.93	2.47	3.063 (5)	122
C22—H22B···O7^iv	0.97	2.41	3.353 (5)	166

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Pr₂(C₈H₇O₃)₆(C₁₂H₈N₂)₂]
M_r	1549.04
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	20.204 (4), 8.499 (4), 20.799 (3)
β (°)	107.198 (6)
V (Å³)	3411.8 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.49
Crystal size (mm)	0.33 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.642, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	27763, 7712, 5037
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 0.90
No. of reflections	7712
No. of parameters	452
No. of restraints	144
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.64

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Selected geometric parameters (Å, º) top

Pr1—O1	2.489 (2)	Pr1—O7	2.409 (3)
Pr1—O2ⁱ	2.535 (2)	Pr1—O8ⁱⁱ	2.545 (3)
Pr1—O4	2.565 (2)	Pr1—N1	2.753 (3)
Pr1—O5	2.817 (3)	Pr1—N2	2.720 (3)
Pr1—O5ⁱ	2.449 (2)

O1—Pr1—O4	73.62 (8)	O5—Pr1—N1	102.34 (9)
O1—Pr1—O5	65.11 (8)	O7—Pr1—N1	77.09 (9)
O1—Pr1—O7	145.88 (9)	O1—Pr1—N2	81.11 (9)
O4—Pr1—O5	48.17 (8)	O4—Pr1—N2	74.08 (9)
O4—Pr1—O7	138.84 (9)	O5—Pr1—N2	118.22 (8)
O5—Pr1—O7	139.57 (8)	O7—Pr1—N2	96.74 (9)
O1—Pr1—N1	127.55 (9)	N1—Pr1—N2	59.78 (10)
O4—Pr1—N1	63.48 (9)

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.93	2.46	3.147 (5)	130
C10—H10···O4ⁱⁱⁱ	0.93	2.34	3.211 (5)	156
C12—H12···O8ⁱⁱ	0.93	2.47	3.063 (5)	122
C22—H22B···O7^iv	0.97	2.41	3.353 (5)	166

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z.

Acknowledgements

This work was supported by the Science and Technology Bureau of Jian, Jiangxi Province, China (grant No. 20052817).

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Volume 64| Part 2| February 2008| Pages m317-m318

doi:10.1107/S1600536807068614

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Retracted: catena-Poly[[(1,10-phenanthroline-κ2N,N′)praseodymium(III)]-di-μ-phen­oxy­acetato-κ4O:O′-[(1,10-phenanthroline-κ2N,N′)praseodymium(III)]-di-μ-phen­oxy­acetato-κ4O:O′-di-μ-phen­oxy­acetato-κ3O,O′:O;κ3O:O,O′]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Retracted: catena-Poly[[(1,10-phenanthroline-κ²N,N′)praseodymium(III)]-di-μ-phenoxyacetato-κ⁴O:O′-[(1,10-phenanthroline-κ²N,N′)praseodymium(III)]-di-μ-phenoxyacetato-κ⁴O:O′-di-μ-phenoxyacetato-κ³O,O′:O;κ³O:O,O′]